Platanosides from Platanus × acerifolia: New molecules, SAR, and target validation of a strong lead for drug-resistant bacterial infections and the associated sepsis

Theodor Bilharz Research Institute

Bibliographic Information

Authors: Wu X.-Y.; Zhao Z.-Y.; Osman E.E.A.; Wang X.-J.; Choo Y.-M.; Benjamin M.M.; Xiong J.; Hamann M.T.; Luo C.; Hu J.-F.

Journal: Bioorganic Chemistry

Publisher: Academic Press Inc.

Publication Date: February 2024

Volume / Issue: Volume 143

Article No.: 107103

ISSN: 452068

DOI: 10.1016/j.bioorg.2024.107103

Scopus: View on Scopus

PubMed: 38211549

Document Type: Article

Access: All Open Access; Green Open Access

Authors and Affiliations

Wu X.-Y., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Evolutionary Ecology and Conservation, Taizhou University, Zhejiang, 318000, China, School of Pharmacy, Fudan University, Shanghai, 201203, China, Shanghai Skin Disease Hospital, Tongji University School of Medicine, Shanghai, 200443, China; Zhao Z.-Y., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Evolutionary Ecology and Conservation, Taizhou University, Zhejiang, 318000, China, School of Pharmacy, Fudan University, Shanghai, 201203, China; Osman E.E.A., Department of Medicinal Chemistry, Theodor Bilharz Research Institute, Kornaish El-Nile St., Giza, 12411, Egypt; Wang X.-J., School of Pharmacy, Lanzhou University, Gansu, Lanzhou, 730000, China, Colleges of Pharmacy and Medicine, Medical University of South Carolina, Charleston, 29425-5700, United States; Choo Y.-M., Chemistry Department, Faculty of Science, University of Malaya, Kuala Lumpur, 50603, Malaysia; Benjamin M.M., Colleges of Pharmacy and Medicine, Medical University of South Carolina, Charleston, 29425-5700, United States; Xiong J., School of Pharmacy, Fudan University, Shanghai, 201203, China; Hamann M.T., Colleges of Pharmacy and Medicine, Medical University of South Carolina, Charleston, 29425-5700, United States; Luo C., State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai, 201203, China; Hu J.-F., Institute of Natural Medicine and Health Products, School of Pharmaceutical Sciences, Zhejiang Provincial Key Laboratory of Plant Evolutionary Ecology and Conservation, Taizhou University, Zhejiang, 318000, China, School of Pharmacy, Fudan University, Shanghai, 201203, China, Colleges of Pharmacy and Medicine, Medical University of South Carolina, Charleston, 29425-5700, United States

Abstract

Three undescribed (1–3) and nine known (4–12) platanosides were isolated and characterized from a bioactive extract of the May leaves of Platanus × acerifolia that initially showed inhibition against Staphylococcus aureus. Targeted compound mining was guided by an LC-MS/MS-based molecular ion networking (MoIN) strategy combined with conventional isolation procedures from a unique geographic location. The novel structures were mainly determined by 2D NMR and computational (NMR/ECD calculations) methods. Compound 1 is a rare acylated kaempferol rhamnoside possessing a truxinate unit. 6 (Z,E-platanoside) and 7 (E,E-platanoside) were confirmed to have remarkable inhibitory effects against both methicillin-resistant S. aureus (MIC: ≤ 16 μg/mL) and glycopeptide-resistant Enterococcus faecium (MIC: ≤ 1 μg/mL). These platanosides were subjected to docking analyses against FabI (enoyl-ACP reductase) and PBP1/2 (penicillin binding protein), both of which are pivotal enzymes governing bacterial growth but not found in the human host. The results showed that 6 and 7 displayed superior binding affinities towards FabI and PBP2. Moreover, surface plasmon resonance studies on the interaction of 1/7 and FabI revealed that 7 has a higher affinity (KD = 1.72 μM), which further supports the above in vitro data and is thus expected to be a novel anti-antibacterial drug lead. © 2024 Elsevier Inc.

Keywords

Antibacterial; Enterococcus faecium; Molecular docking; Molecular ion networking (MoIN); Platanosides; Platanus × acerifolia; Staphylococcus aureus; Structure-activity relationship (SAR); Target validation; Anti-Bacterial Agents; Chromatography, Liquid; Enoyl-(Acyl-Carrier-Protein) Reductase (NADH); Glycosides; Humans; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Phenols; Sepsis; Staphylococcal Infections; Tandem Mass Spectrometry; glycopeptide; kaempferol; penicillin binding protein; plant medicinal product; antiinfective agent; enoyl acyl carrier protein reductase (NADH); glycoside; phenol derivative; platanoside; antibacterial activity; Article; bacterial growth; bacterial infection; bacterial strain; binding affinity; binding assay; in vitro study; isolation and purification; isolation procedure; liquid chromatography-mass spectrometry; methicillin resistant Staphylococcus aureus; nonhuman; nuclear magnetic resonance; plant leaf; structure activity relation; surface plasmon resonance; chemistry; human; liquid chromatography; microbial sensitivity test; Staphylococcus infection

Citation Information

Scopus Citations: 8

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